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I often wonder about #2 (can an emoticon's smile function as a closing parenthesee? ;^)
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J.R.May 15 '12 at 22:31

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Find an authority that matches your prejudice, and you'll be happy. Then I can find one (or deny the existence of one) that matches mine. And neither of us is wrong.
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Colin FineMay 15 '12 at 22:42

Bringhurst, p 71: “4.4.2 Avoid overpunctuating lists. .. If the numbers are made visible either through positions (e.g., by hanging them in the margin) or through prominence (e.g., by setting them in a contrasting fact), additional punctuation – extra periods, parentheses or the like – should rarely be required.”
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tchristMay 16 '12 at 3:08

To avoid the emoticon/parenthesis problem, if I have a parenthetical with an emoticon, I use square brackets instead of parentheses [like this :) ] and I make sure to add a space before the closing mark. I suppose you can also do a right-to-left smiley (like this (: ) but unless you're accustomed to reading Hebrew or Arabic, it might give you eyeball whiplash.
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Lauren IpsumMay 16 '12 at 17:39

4 Answers
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Asking for a ruling on a point of style like this is generally pretty futile in English. There is no central authority. However, style manuals or internal style sheets can provide guidance, even though different ones will have varied answers.

Which answer you use depends on what document you're writing, and whether there's a style sheet that covers it. (Many corporations have internal style sheets.) If the document you're working on is to be published, one of the following general style guides (i.e., not an in-house, corporation- or publication-specific guide) may help:

The closest to a solid ruling on this that I found is in the Franklin Covey Style Guide for Business and Technical Communication. Vertical lists use bare numbers followed by periods, with sub-entries using letters in the same format. Inline lists use numbers/letters inside a pair of parentheses: (1), (a), and so on. (1997, pp.158-160)

In running text, a series of items is designated by letters in parentheses: (a) first item, (b) second item, and (c) third item.

The Chicago Manual of Style uses mix of bare numbers and letters, as well as items enclosed by a pair of parentheses as well as a single parenthesis, leaving the exact execution up to the writer/editor. (16th edition, CMOS 6.126 Vertical lists with subdivided items (outlines) - that's a subscriber-only link, I'm afraid.)

The web-centric Yahoo! Style Manual, on the other hand, barely discusses numbered lists at all, assuming that lists on the web will generally be bulleted. However, the entry on lists does have an example of an inline list (embedded in the text of a paragraph) with opening and closing parentheses.

I also consulted The Economist Style Guide, which uses no special formatting for lists (and doesn't even put a period after the numbers in a vertical list). The Copyeditor's Handbook is also silent on the issue.

If you're writing for internal or informal documents (emails or such), just pick a method that appeals to you and stick with it. Personally, I prefer using single brackets in vertical lists and double brackets in inline text, since you're reading up to them; but that's just a personal preference.

And one last thing: Smiley faces at the end of a parenthetical sentence will be awkward no matter how you handle them. I suggest rewriting to avoid this.

The APA format is to use bullets, but the use of a single parenthesis is also a standard elsewhere. Use of two parentheses is used far less frequently. The purpose of parentheses in this situation is purely to offset the list item, not to group words into a parenthetical clause as it is used in the English language.